1-Hexanol → 3-Hexyloxypropylene glycol

HRID 1077097Notes

Reaction equation

HRID 1077097 reaction equation
C[O-].[Na+].[CH2:4]([OH:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C([O:15][CH2:16][CH:17]1[O:19][CH2:18]1)CCC.ClCl>CO.CCOCC>[CH2:4]([O:10][CH2:18][CH:17]([CH2:16][OH:15])[OH:19])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 81031-HexanolHCID 17049Butyl glycidyl etherHCID 24526ChlorineHCID 10942334Sodium Methoxide

Product 1

HCID 112290943-Hexyloxypropylene glycol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
155 °C

Procedure

4.7g of a solution containing 22.7% sodium methylate in methanol is added to 61.2g of dehydrated n-hexanol. The methanol is eliminated by heating the mixture to 155°C. After cooling the mixture to 130°C, 39g of tertio-butyl-glycidyl-ether is introduced gradually over a two hour and 50 minute period. This ether has a boiling point of 87°-88°C under 88 mm of mercury and a purity of 95% as determined by measurement of the epoxide function. The secondary products which it contains are chlorinate derivatives having a chlorine content of 0.58%. The reaction is completed by heating the mixture at reflux for one hour.

Workup

  1. temperatureAfter cooling the mixture to 130°C
  2. temperatureby heating the mixture
  3. temperatureat reflux for one hour

Sources & evidence

ORD record
ord-e05f6fd97ac4472a840aab8045840f8c
Source dataset
uspto-grants-1976_05
Patent number
US03959390

Reaction notes

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